How to sell to enterprise clients

One large company could be worth more than all your small customers together. But your contact goes quiet, nobody says who signs, and a 200-question security form arrives just when the deal looks close. Here is how to sell to enterprise clients with no sales team and no famous customers: reach many people at many large companies, have their paperwork ready before they ask, and agree every next step in writing.

Do these three things

About 4 to 5 hours a day, every day. Large companies take months to buy, so judge your messages after 2,800 and each deal by its next dated step.

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1. 1Today: pick 300 large companies where your problem is a top-3 priority for one team, and get ready the pack their buyers will ask for: security or quality answers, insurance, company details and a standard contract.
2. 2Every day: send 100 personal messages to people at those companies, up to 3 roles at one company a week, and ask for a 20-minute call about the problem. AI drafts each one; you add one true line about the person.
3. 3Every Sunday: check every open deal against the plan you wrote with the buyer, and chase the step that has no date. Keep at least 10 deals moving, because many large companies stop buying for reasons that have nothing to do with you.

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1. Pick the large companies you can win first, and the small first deal

Write one line that names the kind of large company, the team inside it that has your problem, the moment the problem hurts, and the small first deal you will offer. Then list 300 companies that fit it. It is your ideal customer profile, written for large companies.

In this guide, an enterprise is a company with about 1,000 people or more. Do not start with the most famous names. Start where your problem is a top-3 priority for one team this year. A famous company that sees you as "nice to have" will take a year and still say no. The first customer only needs the problem badly and needs to look like the next 20 buyers you want. Say the problem in their words, as your value proposition does.

Keep the first deal small: one team, one site, one region or one product line, for a set number of weeks. A small deal needs fewer people to agree. On your first call, ask what the team can spend without a full review by procurement, the team that runs buying and supplier paperwork. Price the first deal under that number if you can. Work out the full price first with your B2B pricing or SaaS pricing, so the small deal is a part of it, not a discount.

[Your company] helps the [team] at [kind of company] with [size] people who [the moment the problem hurts].The first deal is [one team / one site / one product line] for [number] weeks, at [price], counted toward a [12-month] contract.

Then build a list of 300 companies in a Google Sheet. Give ChatGPT or Claude your line and ask it to suggest companies from public sources: industry association member lists, trade press, stock market lists and "largest companies in [industry]" rankings. Add the large companies your competitors name as customers on their own websites; your competitor analysis lists them. Check each one yourself before it goes in. For each company, write which team has the problem and one true, recent fact, such as a launch, a new site or a hiring push. 300 is the number that keeps 100 messages a day going for a month in step 4.

If you run a SaaS: look at your own signups first. Anyone who signed up with an email address at a large company is a way in. The first deal is a paid pilot for one team, not a licence for the whole company.

If you run a B2B company that makes or supplies a product: the first deal is a trial order for one product line or one site. If large buyers in your industry only buy through wholesalers, find a distributor as well.

If you run an agency: the first deal is one project for one brand, product or region, with a scope of work that says exactly what is in it.

If you run a D2C store: "enterprise" for you is usually a retailer or a large corporate order. For shops and chains, get your product into retail stores. This guide fits large corporate orders, such as staff gifts.

• Tool: Google Sheets, and ChatGPT or Claude to suggest companies. Free to start.
• Time: 1 hour 30 minutes for the line and the first 100 companies, then 45 minutes for each next 100.
• You will have: one line, and a sheet with 300 companies, each with the team that has the problem and one fact.
• It worked if: you can name the team with the problem at all 300 companies. If you cannot find 300, your line is too narrow: widen the kind of company, not the problem.
• Common mistake: chasing the 5 biggest names in your industry. They have the longest reviews and the least need for a small supplier.

2. Build the pack enterprise buyers will ask for before the first call

Put every document that a large company's procurement, security and legal teams will ask for into one folder before your first call. Then a keen buyer never waits weeks for your paperwork.

Procurement now decides in more than half of business purchases: Forrester found procurement is a decision maker in 53% of buying cycles in January 2026. The founders who lose enterprise deals often lose them here, at week 8, waiting on a form. Build the pack once:

1. 1

   Company and tax details

   Your legal name, address, company number, bank letter and tax form. In the US that is a W-9; a supplier outside the US selling to a US company usually fills in a W-8BEN-E.

2. 2

   Insurance certificate

   Ask an insurance broker for a quote and a certificate of insurance. Procurement teams commonly ask for general liability of $1 million or more, professional liability, and cyber liability if you handle their data, with the buyer named on the certificate.

3. 3

   Security answers

   Write a public security page on your website: what data you hold, where it is stored, who can see it, the outside services that touch it, a security contact, and what you do not have yet. Write 2 to 3 page policies from the 36 free SANS templates (updated February 2026). Then fill in the Cloud Security Alliance's CAIQ-Lite once: 138 standard questions, released January 2026, free with an account. It becomes your answer bank. Later, you can fill in the full CAIQ and publish it on the CSA's registry as a free STAR Level 1 self-assessment.

4. 4

   An answer on AI

   Write one plain answer on which AI services you use and whether customer data trains any model. Buyers ask now: 89% of purchases in 6sense's 2025 study included AI features, and the 2026 version of the SIG questionnaire added AI questions.

5. 5

   Standard contract

   Your standard terms (often called an MSA, the main agreement that later orders sit under), an order form, and a data processing agreement (DPA). Under GDPR, a supplier that handles personal data for a company must have a contract with it and its OK for every outside service that touches that data. Pay a lawyer to read your terms once.

6. 6

   Two references

   Ask your current customers if a buyer may call them for 15 minutes. References are the social proof large buyers trust most. Write one short case study, even if the client stays unnamed, and collect testimonials.

SOC 2, an audit report that says an outside auditor checked your security: do not buy one before a deal needs it. It costs about $10,000 to $30,000 a year and about 200 hours of work. Founders on Hacker News in 2026 report closing large buyers with a filled-in questionnaire and honest documents instead. If a buyer still insists, agree in the contract the date you will have it, and start the audit once that contract or a signed letter of intent pays for it. Never write "SOC 2 in progress" unless you have signed with an auditor.

If you run a SaaS: large buyers often ask for single sign-on (SSO), logging in with the company's own work account. Add it when a deal asks for it, not before. WorkOS charges $125 a month per company connection.

If you run a B2B company that makes or supplies a product: the supplier form asks about quality, certificates, capacity and a backup supplier more than about software security. Ask on the first call which certificates the buyer requires. Do not pay for a certificate until a buyer names it.

If you run an agency: professional liability insurance matters most. Expect the security questions when you will log in to their ad accounts or handle their customers' data.

• Tool: a Google Drive folder, the free SANS templates, the free CAIQ-Lite, an insurance broker and a lawyer for one read of your terms.
• Time: about 2 days, once. After that, 30 minutes to add each new question to the bank.
• You will have: one folder with every document, and a public security or quality page.
• It worked if: you can send any document within 1 hour of being asked, and your bank already answers at least 9 of every 10 questions on the next questionnaire.
• Common mistake: answering "yes" to everything to look bigger. Security reviewers check, and a false yes ends the deal later. "No, and here is what we do instead" keeps it moving.

3. Name 10 people at each company and ask for introductions first

For each of your 300 companies, find 10 people across 5 roles. Then send your list to everyone you know and ask who they know there. 3,000 names is one month of messages at 100 a day.

One person never buys alone at a large company. Forrester's 2026 study found a typical purchase involves 13 people inside the company and 9 outside it, and Gong's 2026 data found won deals of $50,000 to $250,000 had at least 10 people involved. Find these roles at every company:

Search LinkedIn for the company name and each job title, and look at the company's website, press releases and conference speaker lists. Ask ChatGPT or Claude which job titles fill each role at that kind of company, then find the names yourself. Find each person's email the way the cold email guides show. Put each person in your lead list with their role and one true fact.

Before you write to strangers, ask for introductions. 6sense's 2025 study of more than 4,000 buyers found 94% had a ranked shortlist of suppliers before they talked to any of them. An introduction is the fastest way onto that list. Buyers also ask AI: Gartner found in March 2026 that 45% of B2B buyers used AI during a recent purchase, so get your company named by ChatGPT as a supplier as well. Send your list of 300 to past colleagues, your current clients, advisors and investors, and ask who they know. Ask partners who already sell to these companies the same question. Networking events and trade shows where these buyers go are the next best way in. Being seen helps too: post about the problem twice a day from your own LinkedIn account, and fix your profile, so the people you message have seen your name and know what you do.

Hi [first name],I'm trying to reach the [team] at a few large [kind of company]. I've attached a list of 300.Do you know anyone at any of them? Even one name helps. If you do, I'll send you a 3-line note you can forward, so it takes you a minute.Thanks,
[Your name]

• Tool: LinkedIn (the free search is enough), Google Sheets, and the free plan of an email finder such as Hunter.
• Time: about 45 minutes a day for 100 new names, and 1 hour once to send the introduction requests.
• You will have: 10 named people at each company, in 5 roles, and a list of the people who can introduce you.
• It worked if: every company has at least 5 names in at least 3 roles, and you get at least 1 introduction for every 30 people you ask.
• Common mistake: writing only to the chief executive, or only to "Head of Procurement". The person with the problem is where most first deals start.

4. Send 100 personal messages a day across each company's buying group

Send 100 one-to-one messages every day to the people on your list, and ask for a 20-minute call about the problem. Write to at most 3 people at one company in the same week, each in a different role, each with a message about their part of the problem. At a small company you write to one person per company, because one person decides. At a large company many people decide, so you reach each role, but never more than 3 in a week and never with the same text.

100 a day is the point. Instantly's 2026 benchmark found an average reply rate of 3.43%. At 10 a day, you get one reply every 3 days and learn nothing for months. At 100 a day, you get about 3 replies a day.

Rules for writing to a large company:

• A different message for each role. The user hears about the daily problem, the manager about the team's result, the budget owner about cost. Never send the same text to two people at one company, and never copy one person on another's email.
• The senior executive comes later. Write to them after you have talked to someone on their team, around your third contact with the company. Gong's 2026 data found win rates fall about 6% when a deal starts with an executive, and rise about 5% when executives join around the third contact.
• Name a colleague only with their OK. "Maya on your team suggested I write" works only if Maya said yes.
• Follow up 3 times, on day 3, day 7 and day 14, in the same thread, with something new each time. Stop the moment someone says no.

Let AI draft. Paste 10 rows at a time into ChatGPT or Claude, each with the person's role and one true fact, plus the template below. Read each draft, make the first line true and about them, then send it. That is about a minute a message.

Send from a safe setup. If you email more than about 50 strangers a day, set up second domains and warm them up first, with SPF and DKIM on each, so your main email stays safe. In the US, every cold email needs your postal address and a way to say no. On LinkedIn, send about 15 connection requests a day: LinkedIn limits invitations, and a block usually lasts a week. Spread the rest of the 100 across LinkedIn messages to people you are connected with, and email. If you like the phone, cold calls count toward the 100 too.

Subject: [their problem, in 3–5 words]Hi [first name],[One true line about them or their team: a launch, a new site, something they said.]I run [your company]. We help [team] at companies like [their company] with [the problem, in their role's words].Could we have 20 minutes this week? I'd like to ask how your team handles [the problem] today. If it's useful, I'll show you what we do at the end.[Your name]
[Your company, postal address]
Not for you? Reply "no" and I won't write again.

• Tool: Gmail or Outlook, LinkedIn, ChatGPT or Claude to draft, and your sheet to log who you wrote to and when to follow up.
• Time: about 2 hours a day for the messages, plus 45 minutes for the new names in step 3 and about 1 hour for the calls they book. Plan those hours into your week first.
• You will have: 700 messages a week, and 2,800 after 4 weeks.
• It worked if: you book at least 1 call for every 100 messages, judged after 2,800. Below that, rewrite the first line and the problem in your step 1 line, then send the next 1,000.
• Common mistake: writing to 10 people at one company on the same day with the same text. It reads as spam, and people forward it to each other. Each message has to be about the person who gets it.

5. Find your champion and write down how the company buys

On every call, find the one person who wants this to happen, ask seven questions about how their company buys, and send a shared plan with names and dates within 24 hours. A champion is someone inside the company who wants what you sell, has some influence, and tells you the truth about what is happening.

Run the call as a discovery call: ask about the problem first, the way you would in a customer interview, and show the product only once you know what they need. Then ask about how they buy. Most founders skip these questions, and that is why deals go quiet at month 3.

What happens if your team does nothing about this for a year?
Who else feels this problem, and who would need to agree?
Who signs for something like this, and what do they need to see?
Is there budget this year? What can your team spend without a full procurement review?
What does a new supplier go through here: security, legal, procurement, quality? How long does each take?
Have you bought from a small company before? What happened?
If this works, by what date would you want it running?

A good champion answers within 2 days, introduces you to the others, and tells you who signs: the decision maker. If your contact will not do any of the three, they like you but they are not your champion. Keep talking to them, and look for another person on the team.

After the call, send the plan as a shared Google Sheet called "[Their company] and [your company]: plan". Ask the champion to correct it. This is often called a mutual action plan. Send a short sales deck with it, for the champion to forward to their boss. They need it, because you will not be in most of the meetings where you are discussed.

Goal: [the result they want], by [date]Step | Who at [their company] | Who at [your company] | Date | Done
Call with the team who has the problem | [name] | [you] | [date] |
Show it to [manager] | [name] | [you] | [date] |
Pilot terms agreed by [who signs] | [name] | [you] | [date] |
Security or quality review | [name] | [you] | [date] |
Legal review of the contract | [name] | [you] | [date] |
Set up as a supplier | [name] | [you] | [date] |
Pilot starts / pilot review | [name] | [you] | [date] |
Contract signed | [name] | [you] | [date] |

• Tool: a Google Sheet shared with the buyer. Free.
• Time: 20 to 30 minutes a call, then 20 minutes to write the plan.
• You will have: one plan per deal, with a name and a date on every step.
• It worked if: every deal has a champion who answers within 2 days, a named person who signs, and a next step with a date.
• Common mistake: demoing to one keen user and calling it a deal. Without the person who signs and the review steps written down, it will stall.

6. Offer a small paid pilot with numbers that decide the next step

Offer a paid pilot: 4 to 12 weeks, with one team, 2 to 4 numbers that decide whether it worked, and a fee that counts toward the first year's contract. Get the person who signs to agree to all of it in writing before you start.

Trials are normal now: Forrester found in 2026 that more than 60% of business buyers use one. A free trial with no end date and no numbers is a beta, not a sale. It rarely becomes a contract, because nobody inside the company is responsible for deciding. Paying even a small fee makes someone responsible.

How to set it up:

• Charge for it. If they say pilots are free, offer to count the whole fee toward the first year. If they still will not pay anything, ask for a signed letter that says what they will buy if the numbers are met.
• 2 to 4 numbers tied to their result, not to your features: "hours spent on X fall from 10 to 4 a week", "boxes delivered in 21 days, with fewer than 1 in 100 misprinted".
• The person who signs agrees to the numbers, the end date and the price of the full contract before it starts.
• Know the review steps first. If security, legal or procurement must approve even a pilot, put those steps on the plan from step 5.

If your website shows prices, add an enterprise line to your pricing page, such as "Pilots for large teams from [price]". Most buyers research alone first: Gartner found in March 2026 that 67% of B2B buyers prefer to buy without a salesperson.

Turn the terms into a proposal the champion can pass around. If they say it must go out to tender, respond to the RFP and ask whether a paid pilot can run while the tender is prepared.

Pilot: [your product or service] for [team] at [their company]
Dates: [start] to [end] ([4–12] weeks)
What we do: [the work, in 3 lines]
What you do: [the people, data or access you give, by when]
It worked if: [number 1], [number 2], [up to 4]
Fee: [price], paid [up front / on start], counted in full toward the first year
If it worked: a [12-month] contract at [price], signed by [name] by [date]
Agreed by: [name of the person who signs], [date]

• Tool: Google Docs.
• Time: about 1 hour to write the terms, then one call to agree them.
• You will have: one page of pilot terms, agreed in writing by the person who signs.
• It worked if: at the end, each number is met or you know exactly why not, and the contract is on the plan with a date.
• Common mistake: a free pilot with no end date and no numbers. It runs for months, the team gets busy, and nobody decides.

7. Get through security, legal and procurement in days, not months

Answer every questionnaire within 2 days from your answer bank, register in the buyer's supplier system the day you are invited, and agree payment and contract terms using the rules below.

Questionnaires. Large buyers send their own spreadsheet or a standard one such as the SIG Lite, about 126 questions. You pay nothing to answer it. Paste the questions into ChatGPT or Claude with your answer bank, ask it to match each question to an answer, and leave blank anything the bank does not cover. Then check every answer yourself. Never let AI write an answer you have not checked: you are signing it. Where you lack something, use the honest-gap answer below. One founder's August 2026 write-up found prepared answers cut a questionnaire from 2 weeks to 2 days.

We do not have [the control] today.
Our risk is smaller because [your size, how your product is built, what data you do not hold].
What we do instead: [specific, checkable steps].
We will have [the control] by [date].

Supplier systems. Procurement will invite you into a supplier portal, such as the Coupa Supplier Portal. Register the day the invite arrives, using the details from your pack. Ask your champion for the purchase order number before you start any work: many large companies do not pay an invoice without one.

Payment terms, the days they take to pay you. Ask for net 30, payment 30 days after your invoice. Accept up to net 60. If they insist on 90 days, ask for the pilot fee up front or raise the price to cover the wait. In the UK, a bill introduced in May 2026 would cap the payment terms large firms give small suppliers at 60 days. It is not law yet, but you can point to it when you ask for shorter terms.

The contract. If they insist on their own contract, have a lawyer read it before you sign. Ask the lawyer to check five things: the cap on what you owe if something goes wrong, promises to cover their losses, who owns the work, how either side can end it, and payment terms. Never accept unlimited liability; ask for a cap tied to the fees they pay you.

• Tool: your answer bank, ChatGPT or Claude to match questions, the buyer's supplier portal, and a lawyer.
• Time: about 4 to 8 hours for your first questionnaire, then 1 to 2 hours each once the bank is full; 1 hour to register as a supplier.
• You will have: every review answered, you set up as a supplier, and a contract you understand.
• It worked if: you never take more than 2 days to answer, and each review closes within 2 weeks.
• Common mistake: waiting for procurement to say what comes next. Every week, ask your champion: "What has to happen next, and who does it?"

8. Every Sunday, check each deal against its plan and count your numbers

Every Sunday, open every deal's plan, check that its next step has a name and a date, and fill in one row of numbers. A large company's buying takes months, so this is how you see progress before the contract.

6sense's 2025 study found large buying cycles took about 10 months on average. Many deals stop for reasons that have nothing to do with you: a new boss, a budget freeze, a reorganisation. So keep at least 10 deals with a champion moving at the same time in your sales pipeline, and judge each one by its next dated step, not by how keen it sounds.

Week | Messages sent | Replies | Calls | Deals with a champion | Deals with a next step and a date | Pilots running | Contracts signedFor each open deal: next step | who | date | days since the champion last replied

The rules:

• A deal with no next date: message your champion today with one question: "What has to happen next, and by when?"
• Champion silent for 14 days: write to 2 other people you have met at the company.
• Silent for 30 days: move it to "later". Follow up once a month with something new, such as a case study or a monthly email, and keep messaging other roles there.
• After 2,800 messages, fewer than 1 call per 100: rewrite your step 1 line or change the kind of company.

When the sheet gets slow, move to a CRM. Write down where each deal came from: introductions, messages, events. Once a month, work out what each deal cost you in hours and money, in your monthly review.

• Tool: Google Sheets.
• Time: about 30 minutes each Sunday.
• You will have: one row a week, and every open deal with its next step.
• It worked if: every open deal has a next step with a name and a date, and you have at least 10 deals with a champion.
• Common mistake: counting how many companies "seem interested". Count dated steps. A deal with no next date is not moving.

When your first contract is signed, ask the champion who else in the company has the same problem. A second team at the same company is often the easiest next deal. To focus on fewer, larger accounts later, run account-based marketing.

Your enterprise sales checklist

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Step 1 · Pick the large companies you can win first

• Write one line: the large companies, the team with the problem, the moment it hurts, and the small first deal.
• List 300 companies that fit the line, with the team and one fact for each.

Step 2 · Build the pack enterprise buyers will ask for

• Put your company details, tax form, insurance certificate, standard contract and two references in one folder.
• Write your security or quality page and policies, and fill in CAIQ-Lite once as your answer bank.

Step 3 · Name 10 people at each company

• Every dayAdd 100 named people at your companies, across the 5 roles.
• Send your list of 300 companies to everyone you know and ask who they know there.

Step 4 · Send 100 personal messages a day

• Every daySend 100 personal messages asking for a 20-minute call.
• Every dayFollow up with everyone who has not replied, up to 3 times.

Step 5 · Find your champion and write down how the company buys

• After every callAsk the seven buying questions and send the shared plan within 24 hours.

Step 6 · Offer a small paid pilot

• Send one page of pilot terms and get the person who signs to agree to them.

Step 7 · Get through security, legal and procurement

• For every reviewAnswer each questionnaire or supplier form within 2 days from your answer bank.
• Register as a supplier, agree payment terms, and have a lawyer read the contract.

Step 8 · Check each deal against its plan every Sunday

• Every SundayFill in the Sunday row and check every deal's next step.
• After 2,800 messagesJudge your messages and change the line or the companies if you get fewer than 1 call per 100.

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